Founding Head of GTM & Demand Gen

AUTOPILOT; Chicago (IL); On-site; USD 100,000 - 200,000; Full time

Benefits offered by this job

Base Salary + Annual bonus potential

Equity: Early-stage ownership through

100% Employer-covered Health, Dental,

401(k) — Company-administered plan

Flexible PTO — Time off as needed

Travel Reimbursement — Reimbursed in

Team & Culture Events — Team offsites,

Job summary

Autopilot is building the next-generation GTM engine in Chicago for an early-stage B2B tech company. We seek our first GTM leader to turn strategy into pipeline, owning demand generation and partnering with Sales, Product, and Leadership to drive predictable revenue growth.

You'll start hands-on, executing while laying the foundations for a scalable marketing organization and eventually mentoring a team as we scale.

Qualifications

• When you build demand generation programs in B2B SaaS, you move fast and measure impact.
• You own strategy and execution in early-stage environments with limited playbooks.
• You translate market insights into messaging, campaigns, and product positioning.

Responsibilities

• Own GTM strategy and demand generation roadmap across enterprise and channel partners.
• Identify new growth opportunities, verticals, and acquisition channels.
• Partner with Sales, Product and Leadership to drive pipeline and revenue.
• Personally build and optimize campaigns across paid media, email, SEO/GEO, content, events.
• Own marketing automation, lifecycle campaigns, and reporting.

Skills

Demand generation

GTM planning

HubSpot

Data analysis

Cross-functional collaboration

Tools

HubSpot

Job description

Location: Chicago, IL Headquarters

Type: Full-time, in office

Company Stage: Early-stage / startup

We're a small, fast-moving team building something genuinely new. The right person for this position is highly organized, naturally prioritizes the work that moves the top line, and doesn't need a fully built playbook to get started. Early-stage startup life means shifting priorities, lean resources, and high expectations — and that energizes you rather than slows you down. If you're looking for a structured corporate environment with defined processes and a large support team, this probably isn't the right fit. Expect to spend roughly 70–80% of your time executing and 20–30% building the strategy, systems, and team. Over time, that balance will shift as you hire and develop the organization. If you want real ownership, real impact, and the chance to build something from the ground up, keep reading.

About Us — Our Mission & Vision

At Autopilot, our mission is to free people up to do what they do best by automating everything else. We are building the infrastructure layer that powers autonomy in motion across the physical world — including sports, fitness, logistics, healthcare, and more. Our systems help robots move, record, deliver, train, and connect in real-world environments that have historically lacked modern tooling. Our values are simple and non-negotiable: Do Good. Have Fun. Make Money. We believe these are mutually reinforcing, and we work hard to uphold them as we grow.

We move fast, operate scrappy, and care deeply about building something that works.

Benefits

You will be eligible to participate in company benefits and perks, which currently include:

• Base Salary + Annual bonus potential
• The total compensation range for this role is $100,000–$200,000. This range reflects total target compensation, which includes base salary and bonus potential. Where a candidate falls within the range depends on factors such as experience and skills.
• Equity: Early-stage ownership through stock options. A chance to build meaningful value as we scale.
• 100% Employer-covered Health, Dental, and Vision Insurance
• 401(k) — Company-administered plan
• Flexible PTO — Time off as needed, coordinated with your team
• Travel Reimbursement — Reimbursed in accordance with company policy, where role-related travel is required
• Team & Culture Events — Team offsites, social events, and company-sponsored activities

Benefits and policies may be updated from time to time at the company's discretion.

The Role

We're looking for our first GTM leader to build and own the company's demand generation engine. You'll be responsible for turning company strategy into pipeline by developing GTM plans, owning demand generation, aligning closely with Sales, and building the systems, reporting, and operating cadence that drive predictable revenue growth. You'll begin as a player-coach, personally executing while building the foundation for a future marketing organization.

What You'll Own

As Autopilot's first GTM leader, you'll build the growth engine that powers our business. This is a true player-coach role — you'll develop the strategy while rolling up your sleeves to execute it. As we grow, you'll build the team, systems, and processes that scale beyond you.

Go-to-Market Strategy & Growth

• Own our GTM strategy and demand generation roadmap across enterprise and channel partners.
• Identify new growth opportunities, verticals, and acquisition channels.
• Partner with Sales, Product and Leadership to drive pipeline and revenue.

Demand Generation & Marketing Execution

• Personally build and optimize campaigns across paid media, email, SEO/GEO, content, events, and emerging channels.
• Own HubSpot marketing automation, lifecycle campaigns, and reporting.
• Manage agencies, vendors, and AI-powered marketing tools to maximize performance.
• Continuously test, learn, and improve marketing performance across every channel.

Content, Analytics & Operations

• Own messaging, positioning, content strategy, and organic growth.
• Build dashboards that measure pipeline, conversion, and marketing ROI.
• Present actionable insights and recommendations to leadership.

What We're Looking For

You have a bias toward action. You'd rather launch, measure, and improve than spend weeks perfecting a plan. You have strong opinions, held loosely. You'll make decisions quickly, use data to validate them, and change course when new information suggests a better path.

You're a builder.

• You've built and executed demand generation programs yourself — not just managed agencies or approved strategy.
• You're equally comfortable developing a GTM plan and launching a campaign in HubSpot that same day.
• You thrive in early-stage environments where ownership is high and playbooks don't exist yet.
• You're resourceful. You know how to deliver results without a large budget or a large team.

You're accountable to outcomes.

• You think like an owner — you care about revenue, unit economics, CAC, payback, and building a predictable growth engine.
• You care about pipeline and revenue, not vanity metrics.
• You use data to prioritize, optimize, and make decisions.
• When something isn't working, you don't wait to be told — you figure it out and fix it.
• You constantly seek customer feedback and translate market insights into better messaging, campaigns, and product positioning.
• You know how to prioritize the few initiatives that will multiply your impact.

You're fluent in the modern marketing stack.

• HubSpot is second nature to you.
• You've successfully managed paid campaigns across Google and Meta.
• You leverage AI tools like ChatGPT or Claude to improve speed, creativity, and execution.
• Experience with tools like Clay, Apollo, BigQuery, Asana, or similar platforms is a plus.

Experience

• 7+ years building demand generation or growth programs in B2B SaaS or technology.
• Experience at an early-stage or high-growth company where you've built programs from scratch.
• Demonstrated success generating measurable pipeline and revenue growth.
• Experience owning strategy while remaining hands-on in execution.